TWI842016B - 合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物 - Google Patents

合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物 Download PDF

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Publication number: TWI842016B
Authority: TW; Taiwan
Prior art keywords: terephthalic acid; recycled plastic; monomer composition; monomer; mol
Prior art date: 2021-07-19

Application number

TW111126859A

Other languages

English (en)

Chinese (zh)

Other versions

TW202313550A (zh

Inventor

朴泰承

金貞男

黃智煥

洪武鎬

Original Assignee

南韓商Ｌｇ化學股份有限公司

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2021-07-19

Filing date

2022-07-18

Publication date

2024-05-11

2021-07-19 Priority claimed from KR1020210094472A external-priority patent/KR20230013564A/ko

2021-07-19 Priority claimed from KR1020210094470A external-priority patent/KR20230013562A/ko

2021-07-19 Priority claimed from KR1020210094471A external-priority patent/KR20230013563A/ko

2021-07-19 Priority claimed from KR1020210094473A external-priority patent/KR20230013565A/ko

2022-07-18 Application filed by 南韓商Ｌｇ化學股份有限公司 filed Critical 南韓商Ｌｇ化學股份有限公司

2023-04-01 Publication of TW202313550A publication Critical patent/TW202313550A/zh

2024-05-11 Application granted granted Critical

2024-05-11 Publication of TWI842016B publication Critical patent/TWI842016B/zh

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239000000178 monomer Substances 0.000 title claims abstract description 263
239000000203 mixture Substances 0.000 title claims abstract description 165
229920003023 plastic Polymers 0.000 title claims abstract description 165
239000004033 plastic Substances 0.000 title claims abstract description 165
238000000034 method Methods 0.000 title claims abstract description 75
239000004014 plasticizer Substances 0.000 title claims abstract description 20
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 688
229920001577 copolymer Polymers 0.000 claims abstract description 113
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 97
230000002194 synthesizing effect Effects 0.000 claims abstract description 37
239000002245 particle Substances 0.000 claims abstract description 22
238000012691 depolymerization reaction Methods 0.000 claims description 83
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 64
238000001953 recrystallisation Methods 0.000 claims description 62
239000007795 chemical reaction product Substances 0.000 claims description 55
239000003960 organic solvent Substances 0.000 claims description 55
239000002904 solvent Substances 0.000 claims description 52
150000002009 diols Chemical class 0.000 claims description 51
239000000047 product Substances 0.000 claims description 42
238000005406 washing Methods 0.000 claims description 41
229920006346 thermoplastic polyester elastomer Polymers 0.000 claims description 40
229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 17
238000006386 neutralization reaction Methods 0.000 claims description 17
239000000155 melt Substances 0.000 claims description 15
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238000001816 cooling Methods 0.000 claims description 14
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239000012535 impurity Substances 0.000 abstract description 56
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 93
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239000013078 crystal Substances 0.000 description 23
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
239000005977 Ethylene Substances 0.000 description 8
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 8
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KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 8
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YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
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238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
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239000003463 adsorbent Substances 0.000 description 3
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OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 3
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238000001179 sorption measurement Methods 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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150000001279 adipic acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
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229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
PEIIRIVDOVFUIW-UHFFFAOYSA-N bis(7-methyloctyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C=C1 PEIIRIVDOVFUIW-UHFFFAOYSA-N 0.000 description 2
DUQLDVZUQAAAMU-UHFFFAOYSA-N bis(8-methylnonyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C=C1 DUQLDVZUQAAAMU-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
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238000004821 distillation Methods 0.000 description 2
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238000005259 measurement Methods 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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239000004800 polyvinyl chloride Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
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238000000926 separation method Methods 0.000 description 2
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239000005909 Kieselgur Substances 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
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150000004982 aromatic amines Chemical class 0.000 description 1
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238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
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238000010102 injection blow moulding Methods 0.000 description 1
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238000002844 melting Methods 0.000 description 1
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239000011259 mixed solution Substances 0.000 description 1
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239000005022 packaging material Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
- C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/14—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with steam or water
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling

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Polymerisation Methods In General (AREA)

TW111126859A 2021-07-19 2022-07-18 合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物 TWI842016B (zh)

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KR10-2021-0094470		2021-07-19
KR1020210094472A KR20230013564A (ko)	2021-07-19	2021-07-19	재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 성형품 및 가소제 조성물
KR10-2021-0094473		2021-07-19
KR10-2021-0094471		2021-07-19
KR10-2021-0094472		2021-07-19
KR1020210094470A KR20230013562A (ko)	2021-07-19	2021-07-19	재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 성형품 및 가소제 조성물
KR1020210094471A KR20230013563A (ko)	2021-07-19	2021-07-19	재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 성형품 및 가소제 조성물
KR1020210094473A KR20230013565A (ko)	2021-07-19	2021-07-19	재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 성형품 및 가소제 조성물

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TW111126872A TWI820801B (zh)	2021-07-19	2022-07-18	合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物
TW111126782A TWI829248B (zh)	2021-07-19	2022-07-18	合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物
TW111126773A TWI865893B (zh)	2021-07-19	2022-07-18	合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物

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TW111126782A TWI829248B (zh)	2021-07-19	2022-07-18	合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物
TW111126773A TWI865893B (zh)	2021-07-19	2022-07-18	合成再生塑膠之單體組成物、其製備方法以及使用其所製之再生塑膠、模製物與塑化劑組成物

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US (4)	US20230357495A1 (de)
EP (4)	EP4206268A4 (de)
JP (5)	JP2023544007A (de)
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WO2023003280A1 (ko)	2023-01-26
EP4206269A4 (de)	2025-04-09
EP4206270A4 (de)	2025-04-09
CN116323547A (zh)	2023-06-23
TW202313550A (zh)	2023-04-01
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JP2023544008A (ja)	2023-10-19
EP4206269A1 (de)	2023-07-05
JP2023543230A (ja)	2023-10-13
JP7791878B2 (ja)	2025-12-24
WO2023003277A1 (ko)	2023-01-26
US20230383052A1 (en)	2023-11-30
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JP2023543768A (ja)	2023-10-18
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US20230357495A1 (en)	2023-11-09
JP2023544007A (ja)	2023-10-19
WO2023003279A1 (ko)	2023-01-26
CN116368120A (zh)	2023-06-30
US20230374247A1 (en)	2023-11-23
WO2023003278A1 (ko)	2023-01-26
TW202309165A (zh)	2023-03-01
US20230374250A1 (en)	2023-11-23
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